Supposing, for example, a user had added an assignee earlier in the workflow. Later I need that user to remember to update the assignee to a different user at a particular transition. Is this possible?
Sure. It's possible.
1. Specify a condition with a Script Runner script for the transition so that it is only visible if the user updates the assignee.
2. Specify a transition screen which contains the assignee field. Then using the Script Runner plugin you could write a validator which would check to make sure that the assignee on the transition screen is not the same as the previous assignee.
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